Discovery of potent carbonic anhydrase and acetylcholine esterase inhibitors: Novel sulfamoylcarbamates and sulfamides derived from acetophenones

Akıncıoğlu, Akın; Akıncıoğlu, Hülya; Gülçın, İlhami; Durdağı, Serdar; Supuran, Claudiu T.; Göksu, Süleyman

doi:10.1016/j.bmc.2015.04.019

Cited by 140 publications

(105 citation statements)

References 77 publications

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“…General procedure for the synthesis of carbamates: benzyl(4,6-dimethoxy-2,3-dihydro-1H-inden-2-yl) carbamate (10) Carboxylic acid 7 (0.45 g, 2.02 mmol) was dissolved in benzene (30 mL). NEt 3 (0.34 mL, 2.43 mmol) and DPPA (diphenylphosphoryl azide) (0.52 mL, 2.43 mmol) were added to this solution, respectively, and refluxed for 4 h. Then, benzyl alcohol (0.63 mL, 6.07 mmol) was added to this mixture and refluxed for 30 h. At the end of the reaction time, the benzene was evaporated.…”

Section: General Informationmentioning

confidence: 99%

“…Human carbonic anhydrase isoenzymes (hCA I and II) and acetylcholine esterase (AChE) inhibition profile of carbamate derivatives (10)(11)(12)(13)(14)(15)(16) …”

Section: Declaration Of Interestmentioning

confidence: 99%

“…Besides these drugs, the synthesis and biological evaluation of some carbamates have also been reported, e.g. anticancer 6 , HIV protease inhibition 7 , antimicrobial properties 8 , b-secretase inhibition 9 , CA and AChE inhibitory effects of carbamates and sulfamoylcarbamates have been investigated by different research groups [10][11][12] . Carbon dioxide (CO 2 ) and bicarbonate (HCO 3 À ) are essential components in living organism.…”

Section: Introductionmentioning

confidence: 99%

“…Therefore, here we focused on the synthesis of some novel carbamates (10)(11)(12). Then, we investigated AChE and hCA I, and II isoenzymes inhibitory properties of carbamates (10-16) for the first time.…”

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confidence: 99%

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Synthesis and inhibitory properties of some carbamates on carbonic anhydrase and acetylcholine esterase

Yılmaz

Akbaba

Özgeriş

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of carbamate derivatives were synthesized and their carbonic anhydrase I and II isoenzymes and acetylcholinesterase enzyme (AChE) inhibitory effects were investigated. All carbamates were synthesized from the corresponding carboxylic acids via the Curtius reactions of the acids with diphenyl phosphoryl azide followed by addition of benzyl alcohol. The carbamates were determined to be very good inhibitors against for AChE and hCA I, and II isoenzymes. AChE inhibition was determined in the range 0.209-0.291 nM. On the other hand, tacrine, which is used in the treatment of Alzheimer's disease possessed lower inhibition effect (K i : 0.398 nM). Also, hCA I and II isoenzymes were effectively inhibited by the carbamates, with inhibition constants (K i ) in the range of 4.49-5.61 nM for hCA I, and 4.94-7.66 nM for hCA II, respectively. Acetazolamide, which was clinically used carbonic anhydrase (CA) inhibitor demonstrated K i values of 281.33 nM for hCA I and 9.07 nM for hCA II. The results clearly showed that AChE and both CA isoenzymes were effectively inhibited by carbamates at the low nanomolar levels.

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Section: General Informationmentioning

confidence: 99%

“…Human carbonic anhydrase isoenzymes (hCA I and II) and acetylcholine esterase (AChE) inhibition profile of carbamate derivatives (10)(11)(12)(13)(14)(15)(16) …”

Section: Declaration Of Interestmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Synthesis and inhibitory properties of some carbamates on carbonic anhydrase and acetylcholine esterase

Yılmaz

Akbaba

Özgeriş

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…In humans, a-CAs are diffused in different tissues including the blood, kidneys, gastrointestinal tract, reproductive tract, the nervous central system, eyes, skin, lungs, etc. [33][34][35][36][37] . Two cytosolic human CA isoforms (hCA I, and II) are widespread throughout the human body and are drug targets for clinically used diuretics, anticonvulsants and antiglaucoma drugs [38][39][40][41][42] .…”

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confidence: 99%

Synthesis of N-alkyl (aril)-tetra pyrimidine thiones and investigation of their human carbonic anhydrase I and II inhibitory effects

Sujayev

Köse

Garibov

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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Pd(II)‐Catalyzed, γ‐C(sp²)−H Alkoxylation in α‐Methylbenzylamine, Phenylglycinol, 3‐Amino‐3‐Phenylpropanol Toward Enantiopure Aryl Alkyl Ethers

et al. 2022

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This paper reports the synthesis of enantiopure aryl alkyl ethers via the Pd(II)-catalyzed picolinamide-aided γ-C(sp 2 )À H alkoxylation of various enantiopure α-alkylbenzylamine derivatives using alcohols. Enantiopure α-methylbenzylamines and amino alcohol substrates such as 2amino-2-phenylethanol (phenylglycinol) and 3-amino-3-phenylpropanol were subjected to the γ-C(sp 2 )À H alkoxylation (etherification) with alcohols using PIDA. α-Alkylbenzylamines and phenylglycinols are valuable building blocks in organic synthesis and medicinal chemistry research areas. Accordingly, this work has enabled the assembling of various enantiopure ortho-alkoxylated α-methylbenzylamine and 2-amino-2-phenylethanol (phenylglycinol) and 3-amino-3-phenylpropanol derivatives containing aryl alkyl ether functionality. We have shown the utility of ortho-alkoxylated αmethylbenzylamine derivatives for assembling enantiopure α-methylbenzylamine-based sulfamoylcarbamates and carboxamides which are structurally related to the bio-active compounds known in the literature. This work demonstrates the substrate scope elaboration in CÀ H functionalization and etherification through the CÀ O bond-forming process and synthesis of aryl alkyl ether functionality containing enantiopure α-alkylbenzylamines.

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Discovery of potent carbonic anhydrase and acetylcholine esterase inhibitors: Novel sulfamoylcarbamates and sulfamides derived from acetophenones

Cited by 140 publications

References 77 publications

Synthesis and inhibitory properties of some carbamates on carbonic anhydrase and acetylcholine esterase

Synthesis and inhibitory properties of some carbamates on carbonic anhydrase and acetylcholine esterase

Synthesis of N-alkyl (aril)-tetra pyrimidine thiones and investigation of their human carbonic anhydrase I and II inhibitory effects

Pd(II)‐Catalyzed, γ‐C(sp²)−H Alkoxylation in α‐Methylbenzylamine, Phenylglycinol, 3‐Amino‐3‐Phenylpropanol Toward Enantiopure Aryl Alkyl Ethers

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Discovery of potent carbonic anhydrase and acetylcholine esterase inhibitors: Novel sulfamoylcarbamates and sulfamides derived from acetophenones

Cited by 140 publications

References 77 publications

Synthesis and inhibitory properties of some carbamates on carbonic anhydrase and acetylcholine esterase

Synthesis and inhibitory properties of some carbamates on carbonic anhydrase and acetylcholine esterase

Synthesis of N-alkyl (aril)-tetra pyrimidine thiones and investigation of their human carbonic anhydrase I and II inhibitory effects

Pd(II)‐Catalyzed, γ‐C(sp2)−H Alkoxylation in α‐Methylbenzylamine, Phenylglycinol, 3‐Amino‐3‐Phenylpropanol Toward Enantiopure Aryl Alkyl Ethers

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Product

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Pd(II)‐Catalyzed, γ‐C(sp²)−H Alkoxylation in α‐Methylbenzylamine, Phenylglycinol, 3‐Amino‐3‐Phenylpropanol Toward Enantiopure Aryl Alkyl Ethers